17α-Acyloxy-5β-corticoids and 17α-acyloxy-5α-corticoids

Abstract

17α-Acyloxy-5β-pregnanes (I) and 17α-acyloxy-5α-pregnanes (IV) have an excellent activity split providing high topical anti-inflammatory activity with very low systemic side effects.

Description

This is a division of application Ser. No. 117,401, filed Jan. 31, 1980 now U.S. Pat. No. 4,318,853.

The present invention relates to 5α and 5β- 17α-acyloxy corticoids which are useful as topical anti-inflammatory agents for which the essential material constituting a disclosure thereof is incorporated by reference here from U.S. patent application Ser. No. 117,401, filed Jan. 31, 1980, now U.S. Pat. No. 4,318,853.

Claims

1. A 5β-steroid of the formula ##STR1## where R₂ is a hydrogen, fluorine or chlorine atom or methyl group;

R₆ is a hydrogen, fluorine or chlorine atom or methyl group;

R₇ is a hydrogen, fluorine or chlorine atom;

R₉ is a hydrogen, fluorine or chlorine atom;

R₁1 is a chlorine or oxygen atom or hydroxyl group; when R1₁ is a chlorine atom or hydroxyl group the between R₁1 and C₁1 is a single bond in the β configuration and when R₁1 is an oxygen atom the between R₁1 and C₁1 is a double bond;

R₁6α is a hydrogen, fluorine or chlorine atom or methyl group;

R₁6β is a hydrogen atom or methyl group with the proviso that one of R₁6α or R₁6β is a hydrogen atom;

R₁7 is alkyl of 1 through 6 carbon atoms, phenyl, p-methylphenyl, p-carboxyphenyl or p-carboalkoxyphenyl;

R₂1 is a hydrogen, fluorine, chlorine or bromine atom or a --OR₂1α or --OSO₂ CH₃ group;

R₂1α is a hydrogen atom, --COR₂1β or --PO(OH)₂ and pharmaceutically acceptable salts thereof;

R₂1β is alkyl of 1 through 6 carbon atoms, phenyl, p-methylphenyl, or p-carboxyphenyl, p-carboalkoxyphenyl, --CH₂ CH₂ COOH and pharmaceutically acceptable salts thereof;

is a single or double bond; and

indicates the attached group can be in either the α or β configuration.

2. A compound according to claim 1 where R₂ is a hydrogen atom or methyl group.

3. A compound according to claim 2 where R₂ is a hydrogen atom.

4. A compound according to claim 1 where R₆ is a hydrogen or fluorine atom or methyl group.

5. A compound according to claim 4 where R₆ is a hydrogen atom.

6. A compound according to claim 1 where R₇ is a hydrogen or chlorine atom.

7. A compound according to claim 6 where R₇ is a hydrogen atom.

8. A compound according to claim 1 where R₁6α is a hydrogen atom or methyl group.

9. A compound according to claim 1 where R₁6β is a hydrogen atom or methyl group.

10. A compound according to claim 9 where R₁6β is a methyl group.

11. A compound according to claim 1 where R₁7 is alkyl of 1 thru 5 carbon atoms, phenyl, or paramethylphenyl.

12. A compound according to claim 11 where R₁7 is alkyl of 1 thru 4 carbon atoms or phenyl.

13. A compound according to claim 1 where R₂1 is a hydrogen, fluorine, or chlorine atom or a --OR₂1α group where R₂1α is defined in the specification.

14. A compound according to claim 13 where R₂1 is a hydrogen or chlorine atom or --OR₂1α group where R₂1α is --COR₂1β where R₂1β is defined in the specification.

15. A compound according to claim 1 which is 21-chloro-9α-fluoro-11β,17α-dihydroxy-16β-methyl-5.b eta.-pregnane-3,20-dione 17-propionate.